Caught by My Boss Pt. 02

Derick worked me over with his fingers and tongue until he felt satisfied and I felt intoxicated with pleasure. My sissy pussy was buzzing and even after he pulled back I could feel phantom sensations of his tongue eating me out. He somehow kept finding ways to make me even more pliable to his own desires though I had to accept the truth sooner than later that my desires were quite the same if not just a mirror opposite. Derick desired domination and control while I savored the submission and servitude towards him, needles to say, a perfect dynamic. I heard his pants unbuckling and the crinkling of a condom wrapper being opened though I didn't possess the energy to move from my half-slumped position against the window to look. I knew what was coming and was more than ready for it, I had been craving him filling me up all day and was finally about to receive my award for being his good girl. I felt Derick run his cock up and down my crack through the generous amount of saliva that was now covering me before he slapped it on my hole a few times and started to push in.

When I played with myself and my toys I always erred on the side of too much lube and had never managed to play without proper lubricant but the blend of his spit, my lust, and the fact that I had the plug in me all day made my pussy a welcoming receiver for his hard dick. This time around I knew what to expect and yet still caught myself panting as he pushed into me and felt the sensation of just how much his thick cock filled me up. He was exceptionally hard and my hole willingly gave way to him with each small thrust he gave me which at first were only a couple inches past the tip. My lips, still partly numb from the facefucking, formed a drunken smile which turned into a loose 'O' shape as if I was silently screaming when he thrust his entire member into me without warning. His cock seemed able to hit every nerve ending inside me and my body exploded in ecstasy. The ridge of his engorged mushroom head rubbed along my prostate and within two or three thrusts I felt the familiar wash of pleasure roll through my body from the center out. I was primed all day for this moment and even still was surprised at how quickly his cock simply took me over. Every in and out thrust kept the waves coming and if my panties were soaked before, they were utterly flooded now as I was in the midst of a constant and formidable prostate orgasm.

"Mhmm, you even cum multiple times like a proper girl, Andi, look at the mess you're making."

I couldn't bring myself to even answer as I drifted into the euphoria Derick was administering me with his cock, it was so good I felt as though I had no more sensation of different parts of my body and my entire being was simply a form of pure satisfaction and joy. Derick would sporadically slow his pace down, at times to a painfully slow tempo, but without ever letting me slip from this state before he would pick it up again and pound me viciously. I could have carried on like this forever and died happy but Derick slid out of me and turned me from the window. I only had a moment or two to question why he had stopped before he knelt down and grabbed me with both arms behind the knees and stood up with my entire weight held against his broad chest. He kind of tossed me up a couple times to adjust me the way he wanted and pressed forward to pin me against the window again but this time we were facing each other while he cradled me in his arms as I was somewhat bent in half with my ass being the lowest point of me. Leaning his weight into me to keep me up against the window, he reached a hand down and guided his cock back into my wanting pussy. In this position he was not only able to thrust himself into me but also lifted me with his arms and dropped me down to allow me to feel the hardest pummeling I had ever taken and yet I was so worked up that I took it with ease. He continued his barrage on my hole while I had my head thrown as far back as the window would allow, at this point nearly voiceless after how much I had already let out. The only audible sounds were his grunts and the sound of his flesh slapping against mine as he threw me up and down on his cock. I came around at some point and looked towards him only to find him staring at me with an animalistic gaze that caught me off guard. I felt locked in his eyes and used my own to plead him for more and more.

If I had time to process it, I would have been jealous of Derick's stamina as he must have had me pinned against the window taking his cock for thirty minutes alone, not to mention the time he had spent ravaging my mouth and throat. However, all good things must end and he held his eyes locked on me while his grunts and thrusts picked up in speed.

"Your tight little pussy is going to make me cum, Andi." he said, staring me in the face. "Be a good slut and make me cum."

"Yes, sir, please. I want to make you cum and feel good. Please cum for me, sir." I spoke back between my own more feminine grunts.

After a few final powerful strokes he pushed into me as far as he could and dragged my own body down into himself and I felt him spasming which told me he was cumming. He still had the condom on but I felt a non-physical sensation of pleasure inside me knowing that I had just served my purpose with excellence by taking him and letting him spill his seed inside me. I imagined his cum spurting into me and filling me to the brim as he held me there and enjoyed his own orgasm. That feeling was cut short as he snapped out of his bliss and lifted me off his cock to place me on the ground. I stood, or swayed more accurately, in front of him looking up at my boss, my master, my sir with disbelief as I was only now starting to properly accept what he had just put me through. The man took absolute control of me and straight up USED me to please his cock and it felt so right for me. For both of us, I imagined.

Derick grabbed me lightly by the chin and winked at me before he turned and made his way to the bathroom in his office to clean up. I wanted to follow but needed a minute for my brain and body to re-sync and begin controlling myself again.  By the time I got to the bathroom he had finished cleaning up - after all he only had a dick to clean up, I was a mess head to toe - and sidestepped me to allow me in.

"Go ahead and clean up, Andi. I got a bit lost in the moment there so I need to run home but damn... you did well." he said with only a glance my way as he gathered his things from his desk.

"Derick, that was unbelievable. I've never felt anything like that before." I said, only realizing I had called him by name after the sentence left my lips. "Uh, sorry, I mean sir."

"Don't worry about it, I'll see you tomorrow." he allowed me a moment of tenderness as he left the room.

I knew I had soiled my panties but was shocked at just how much cum and precum I had produced when I started cleaning myself up. The panties were soaked through and there were streaks running down my thighs that had half dried into crusty patches on my skin and the stockings I was wearing. It took me another 15 minutes to get myself clean and by the time I was leaving the building I bumped into the overnight security guard who watched the building after hours. We normally never crossed paths so I was thankful to escape any chatting as I passed by him with a nod and made my way home. Despite feeling as though I had already ejaculated a gallon of cum that day, the moment I got home I fished out my biggest dildo and slid it into my ass which was starting to feel the full effect of Derick's pounding. This didn't stop me from jacking myself off another two times before I passed out in bed.

Arriving at work the next day, I noticed Derick's car was absent from the lot and was honestly kind of looking forward to enjoying a normal day without having him around. I couldn't handle another day of tension in the office while I pretended to work with thoughts of his dick and body running through my mind.

Around morning break time, a few people had gathered at the window at the front of the office where mere hours ago I had been slave to our boss' rock hard cock. I heard some snickering and low talking as I tried eavesdropping on what was being said but could not discern anything. I waited a few minutes after the crowd had dispersed to make my way over, wondering what it was that they were so entertained by. As I approached the window the sun came through at the right angle to illuminate a huge smeared mess of what I knew was my spit and drool on the window. There was even a fairly distinct smudge of a hand print and I realized I had totally forgotten to clean the window and by the time the night staff got around to cleaning the sun must have been too low for them to notice anything. My heart raced as I took a subtle glance around but nobody seemed to be looking my way so I quickly distanced myself from the window as if I would have been revealed simply by being near the scene of the crime.

I knew I would have to take care of the window somehow but if anybody saw anything it would give me away even if they didn't know the details, I didn't need anything for people to latch onto and arouse suspicion. I had a good thing going with Derick and I felt we were much closer to the beginning than the end and I would have been lying to myself if I said I didn't want to see where it would take me.